(E)-1-(2,5-dimethoxyphenyl)-3-(4-N,N-dimethylaminophenyl)prop-2-en-1-one | 127034-22-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (E)-1-(2,5-dimethoxyphenyl)-3-(4-N,N-dimethylaminophenyl)prop-2-en-1-one
• 英文别名: 1-(2,5-dimethoxyphenyl)-3-[4-(dimethylamino)phenyl]prop-2-en-1-one；(E)-1-(2,5-dimethoxyphenyl)-3-[4-(dimethylamino)phenyl]prop-2-en-1-one
• CAS: 127034-22-4
• 化学式: C₁₉H₂₁NO₃
• 分子量: 311.381
• InChiKey: WUCNITUBGKKGRG-YRNVUSSQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-1-(2,5-dimethoxyphenyl)-3-(4-N,N-dimethylaminophenyl)prop-2-en-1-one 在 磺酰氯 作用下， 以 四氯化碳 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 1-(2,5-dimethoxyphenyl)-3-[4-(dimethylamino)phenyl]-2-chloroprop-2-en-1-one
  参考文献：
  名称：

  Chalcones: a new class of antimitotic agents

  摘要：

  A series of chalcones was evaluated as antimitotic agents. One of these, (E)-1-(2,5-dimethoxyphenyl)-3-[4-(dimethylamino)phenyl]-2-methyl-2-pr open- 1-one) (73), was found to be an effective antimitotic agent at a concentration of 4 nM in an in vitro HeLa cell test system. When evaluated in experimental tumor models in vivo, this compound exhibited antitumor activity against L1210 leukemia and B16 melanoma.

  DOI：

  10.1021/jm00169a021
• 作为产物：
  描述：

  2,5-二甲氧基苯甲醛 、 二甲氨基苯乙酮 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 以78%的产率得到(E)-1-(2,5-dimethoxyphenyl)-3-(4-N,N-dimethylaminophenyl)prop-2-en-1-one
  参考文献：
  名称：

  Potent antimitotic and cell growth inhibitory properties of substituted chalcones

  摘要：

  A series of substituted chalcones was synthesised and screened for cytotoxic activity against the K562 human leukaemia cell line. (E)-3-(3"-Hydroxy-4"-methoxyphenyl)-2-methyl-1-(3',4',5'-trimethoxyphenyl)-prop-2-en-1-one [IC50 (K562) 0.21 nM] was found to be the most active. A relationship between the conformation and cytotoxicity of the chalcones is discussed. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00162-0

文献信息

• Novel use of compounds of the chalcones class
  申请人：——

  公开号：US20020143064A1

  公开（公告）日：2002-10-03

  Process for inhibiting vascularization of a tumor mass comprising administering, in an amount effective to inhibit vascularization, at least one chalcone of formula (I): 1 wherein: R is chosen from a hydrogen atom, a methyl group, an ethyl group, a chlorine atom, and a bromine atom, A is an NR 1 R 2 group, wherein R 1 and R 2 , which may be identical or different, are each chosen from a methyl group and an ethyl group, and n is an integer equal to 2 or 3.

  一种抑制肿瘤组织血管生成的处理过程，包括给予至少一种化合物，其有效抑制血管生成，该化合物为式（I）至少一种香豆素：1其中：R选自氢原子，甲基基团，乙基基团，氯原子和溴原子，A是NR1R2基团，其中R1和R2，可以相同也可以不同，分别选自甲基基团和乙基基团，n是等于2或3的整数。
• Combretastatin-like chalcones as inhibitors of microtubule polymerization. Part 1: Synthesis and biological evaluation of antivascular activity
  作者：Sylvie Ducki、David Rennison、Meiko Woo、Alexander Kendall、Jérémie Fournier Dit Chabert、Alan T. McGown、Nicholas J. Lawrence

  DOI：10.1016/j.bmc.2009.09.039

  日期：2009.11

  The alpha-methyl chalcone SD400 is a potent inhibitor of tubulin assembly and possesses potent anticancer activity. Various chalcone analogues were synthesized and evaluated for their cell growth inhibitory properties against the K562 human chronic myelogenous leukemia cell line (SD400, IC50 0.21 nM; combretastatin A4 CA4, IC50 2.0 nM). Cell cycle analysis by flow cytometry indicated that these agents are antimitotic (SD400, 83% of the cells are in G(2)/M phase; CA4 90%). They inhibit tubulin assembly at low concentration (SD400, IC50 0.46 mu M; CA4, 0.10 mu M) and compete with [H-3] colchicine for binding to tubulin (8% [H-3] colchicine remained bound to tubulin after competition with SD400 or CA4). Upon treatment with SD400, remarkable cell shape changes were elicited in HUVEC cells, consistent with vasculature damaging activity. (C) 2009 Elsevier Ltd. All rights reserved.
• Synthesis and inhibitory activity of dimethylamino-chalcone derivatives on the induction of nitric oxide synthase
  作者：Javier Rojas、José N Domı́nguez、Jaime E Charris、Gricela Lobo、Miguel Payá、M.Luisa Ferrándiz

  DOI：10.1016/s0223-5234(02)01387-9

  日期：2002.8

  A series of nine dimethylamino-chalcone derivatives (1,3-diaryl-propenones) was synthesized and screened as potential inhibitors of NO and PGE(2) production in the RAW 264.7 macrophage cell line. 4-Dimethylamino-2',5'-dimethoxychalcone (6) was found to be the most potent and dual inhibitor (IC50s, in the submicromolar range) of NO and PGE(2) production. 2',6'-Dimethoxylation appeared to be an effective requirement for selective and potent inhibition of nitric oxide synthase induction as it was confirmed by Western blot analysis. Chalcone (6) at 25 mg kg(-1) by oral route, inhibited significantly the formation of oedema in the carrageenan-induced model of inflammation in mice. (C) 2002 Editions scientifiques et medicales Elsevier SAS. All rights reserved.
• ANDERSON, DAVID B.;SCHMIEGEL, KLAUS K.;VEENHUIZEN, EDWARD L.;TUTTLE, RONA+
  作者：ANDERSON, DAVID B.、SCHMIEGEL, KLAUS K.、VEENHUIZEN, EDWARD L.、TUTTLE, RONA+

  DOI：——

  日期：——
• EDWARDS, MICHAEL L.;STEMERICK, DAVID M.;SUNKARA, PRASAD S., J. MED. CHEM., 33,(1990) N, C. 1948-1954
  作者：EDWARDS, MICHAEL L.、STEMERICK, DAVID M.、SUNKARA, PRASAD S.

  DOI：——

  日期：——